(1S,2S)-(2-苯甲酰氨基-1,2,3,4-四氢萘-1-基)氨基甲酸叔丁酯 | 1061266-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (1S,2S)-(2-苯甲酰氨基-1,2,3,4-四氢萘-1-基)氨基甲酸叔丁酯
• 英文名称: (1S,2S)-(2-benzoylamino-1,2,3,4-tetrahydronaphthalen-1-yl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S,2S)-2-benzamido-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate
• CAS: 1061266-12-3
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: QUWKGWUVTFDPDN-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(2-苯甲酰氨基-1,2,3,4-四氢萘-1-基)氨基甲酸叔丁酯 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 68.0h， 生成
  参考文献：
  名称：

  Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands

  摘要：

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.024
• 作为产物：
  描述：

  1-吡咯甲酸叔丁酯 在 palladium on activated charcoal 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 吡啶 、 (S,S)-(R,R)-C₂-ferriphos-tolyl 、 甲酸铵 、 亚硝酸异戊酯 、 三氯乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 66.17h， 生成 (1S,2S)-(2-苯甲酰氨基-1,2,3,4-四氢萘-1-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands

  摘要：

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.024

文献信息

• Rhodium-Catalyzed Ring-Opening Reactions of N-Boc-azabenzonor­bornadiene with Chiral Amine Nucleophiles Derived from Amino Acids
  作者：Mark Lautens、Yong-Hwan Cho、Nai-Wen Tseng、Hisanori Senboku

  DOI：10.1055/s-2008-1078596

  日期：2008.8

  The rhodium-catalyzed ring-opening of azabenzonorbornadienes with chiral amino nucleophiles derived from amino ­acids such as (S)-proline and (R)-phenylglycine is reported. The desired products were obtained as a mixture of diastereomers, which could be easily separated in high yield. Enantiomerically pure ring-fused nitrogen heterocycles and 1,2-diamines were also obtained by further transformation of the ring-opened products.

  报道了铑催化的氮杂苯并诺波烯与源自氨基酸（如（S）-脯氨酸和（R）-苯基甘氨酸）的手性氨基亲核试剂的环打开反应。所需的产品以二对映体的混合物形式获得，可以高产率地轻松分离。通过对环打开产品的进一步转化，还获得了对映体纯的环融合氮杂杂环和1,2-二胺。